Acetic Acid → 9-Fluoro-8-methyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513630Notes

Reaction equation

HRID 513630 reaction equation
N[C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH3:9])=[CH:4][C:3]=1[S:10]([NH:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[CH:19]2)(=[O:12])=[O:11].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[F:8][C:6]1[CH:7]=[C:2]2[C:3]([S:10](=[O:11])(=[O:12])[NH:13][C:14]3[C:15]2=[CH:16][CH:17]=[C:18]2[C:23]=3[N:22]=[CH:21][CH:20]=[CH:19]2)=[CH:4][C:5]=1[CH3:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 68183310HCID 68183310, compound2×

Product 1

HCID 681833849-Fluoro-8-methyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 15.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-4-fluoro-5-methyl-N-quinolin-8-yl-benzenesulfonamide (Intermediate 299) (340 mg, 1.03 mmol), t-butyl nitrite (0.18 ml, 1.54 mmol), AcOH (3.4 ml) and THF (3.4 ml) gave the title compound (50 mg, 15%) after purification by column chromatography with DCM/MeOH (90:10) as the eluent.

Sources & evidence

ORD record
ord-b156a798adbd4cb1896f45cff55e3d98
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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